The Craigslist Killer Part 3
© 2014 by Nom de Plume

I paid the cabbie and hurried up a few steps to a side entrance to the Palmer House. It was still unlocked, and I let myself in and made my way quickly down a deserted shopping arcade. I was grateful for the solitude, conspicuous as I must have been in my taffeta dress, shawl and stilettos, but I didn’t encounter a soul all the way to a bank of elevators.

My luck ran out when I stepped into a crowded elevator, full of happy revelers on their way to or from a party somewhere in the hotel. I avoided eye contact with a few of the guys who seemed to be taking an interest in me, and noticed that the button for my floor was already lit. So I pushed the button for the next floor, and waited nervously as the waves of happy conversation surrounded me. When I finally got out of the elevator, I walked down the long hallway to the fire stairs, took them down to my floor, and peeked out the door. There was nobody in sight, and I was able to make it down the hall and into my room without incident.

The message light was blinking on my phone on the nightstand! I was sure the Chicago police had tracked me down…nobody else knew I was here, except my secretary, whom I’d called after I changed hotels. With a feeling of dread, I punched the button for messages and prepared myself for the worst: “Mr. xxxxxx, we got a call from the company you were supposed to meet with on Tuesday, and they were hoping that you could stay in Chicago to meet with them on Monday? I checked and it’s okay with the boss, in fact he’s hoping you’ll be able to. Sorry about your weekend! Let me know if you want me to change your flight.”

What a relief! I kicked off my heels and flung myself on the bed, reveling in the sensations of silk and lace against my skin. So I was stuck in Chicago, as a woman! I had one meeting Friday morning as a guy, then I’d be back in skirts and dresses for three whole days….I had a nagging concern that the sooner I cleared out of town the better, what with the cops looking for Gregg’s transgendered killer, but business was business, and I must have been feeling emboldened by my safe return that night.

I fired up my notebook computer and sent an email to my boss and secretary, telling them I’d stay over for the meeting. Then I went to Missy’s account, where I found several more Craigslist responses, and this email from Ron:

Missy,

I’m so sorry about tonight! I don’t know what I was thinking.
I know I’m not in the same league as you, but I guess I was hoping
you could help me. But what I really want you to know is that I was
really attracted to you, and I feel like such an idiot for turning you off
like that. I know you’re leaving Chicago tomorrow, and we’ll probably
never see each other again, but if there’s any way I could have another
chance with you, I promise it will be different next time.

Love,
Ron

Just what I needed! A lovesick crossdresser…who was handsome, classy and rich! What was wrong with me? I stretched out on the bed in my fancy dress and tried to make sense of my situation.

The Chicago police had a very good description of me as a woman, and knew that I’d spent the night on the same floor as the murder victim. Whether they’d tracked me down to the Palmer House was unknown, but I had to assume it was only a matter of time. So the smart play would be to pack up all my female paraphernalia, FEDEX it back to Los Angeles first thing tomorrow morning, and lay low as a man until I left town.

I looked back at my silky legs, girlishly curled over a froth of taffeta. Maybe there was another way….

* * *

Another morning, another early checkout! This time I left my suitcases with the bell captain, promising to retrieve them later in the day. Then it was off to my meeting, a working breakfast in a conference room at a skyscraper on Adams Street. During a dull moment, I typed out this email to Ron on my smartphone:

Ron, Thank you so much for your sweet message, although
I feel that I’m the one who should apologize to you. I just learned that I have to stay over the weekend, so if you want another shot at me, I’d love to try again with you, Missy

The meeting dragged on and on – I’d have missed my flight anyway – and I found myself checking my smartphone surreptitiously under the table. Finally I heard back from Ron:

Missy, I’m so glad you’re still here, of course I want to see you
again! Are you here all weekend? I have to see my son at the ex’s
this afternoon, then I’m free whenever you are. Are you still at
the Palmer House? You’re welcome to stay with me if you’d like,
Ron

That was too easy…I quickly tapped out this reply to Ron:

You’re the best! I’d love to stay with you, are you sure
that’s not too much trouble? What time are you free, oh and what’s your address? I’ll be arriving as a guy, and change when I get there, if that’s okay…

I barely had time to refocus on the business discussion when my smartphone pinged:

Of course that will be wonderful! I’ll be home by four at the latest, the address is xxxxxxx Astor, see you then!

I ignored some annoyed looks from around the table as I responded:

Sounds good, can’t wait!

“Sorry,” I blithely lied to the group. “Had to change my flight. We’re getting a lot done here today!”

* * *

I ate sparingly during the buffet lunch that was hastily provided at the end of our meeting. I’d be back in women’s clothing again in a few hours, and I needed to keep my girlish figure! When I finally escaped, I took a long walk along the Chicago River before I returned to the Palmer House to pick up my bags. As I was leaving the hotel, out of the corner of my eye I spotted a familiar face: one of the two cops who had interviewed me at the Intercontinental was talking to a hotel security guard in the lobby! I turned away and bolted outside before he could see me, and waited nervously until the doorman summoned a cab.

My pulse was returning to normal by the time I got to Ron’s townhouse. He was waiting at the door when I came up the front steps. “Hi,” he said. “I would never have recognized you.”

“Hi back,” I smiled. “Let me do something about that.”

He took one of my bags and led me upstairs to the master bedroom. “Sorry I don’t have a guestroom for you. My son stays here some weekends, although I guess he won’t be back till he gets out of his cast.” I felt very awkward having Ron see me as a guy, and he must have sensed that, because after a brief conversation about his son’s condition, he left me alone and closed the door behind him.

Finally! I put Missy’s suitcase on Ron’s plush king bed and opened it up, removing the only outfit I’d yet to wear in Chicago: my polka dot tieback blouse and my black skirt with crystal pleats. Hesitantly, I peeked into Ron’s oversized walk-in closet, and got a shock: about a third of it was full of suits, slacks and other guy stuff, but the rest was crammed with an amazing array of women’s clothing. Beautiful dresses, long and short…skirts of every kind and color…enough tops to fill a rack at TJ Maxx…shoes of every description, from flats to heels, including several pairs of sexy boots…I was in a daze as I searched for a hanger for my skirt and blouse. After the closet, Ron’s enormous bathroom was almost anticlimactic: a huge marble tub took up an entire wall, with a fabulous selection of bubble baths, creams and lotions along the side. A plush towel and facecloth had been laid out for me on a standing towel rack, and a matching terrycloth bathrobe was hanging nearby.

Stunned, I took off my suit, shirt and tie, and began filling the tub with some of Ron’s scented bath beads. I imagined that Ron wouldn’t have minded if I’d used one of his razors to shave my legs, but I found mine, and gathered up my makeup and other female essentials and set them out by one of the vanity sinks before I lowered myself into a mound of steaming suds. For the first time since my attempted murder, I was able to totally relax as I surrendered to the bliss of a deep, hot bubble bath, soaking my head under water until I couldn’t hold my breath any longer. Then I lazily shaved myself down, luxuriating in the sensation as I contemplated my host’s situation.

Ron may have been a closet crossdresser, but what a closet! There must be tens of thousands of dollars of women’s clothing, shoes and other paraphernalia in there – I was pretty sure I saw several Gucci bags, the real thing, and some Ferragamo shoes. I already knew that he was rich, and that he yearned to share this side of himself with me, but I had so idea of the extent of his obsession. I analyzed his physique from the standpoint of passing as a woman: he was at least six feet tall, and he must weigh close to two hundred pounds. Although I’d only seen him in long sleeves, I could tell that he was very buff, with broad shoulders and manly arms. So his reluctance to go out dressed was understandable, and so sad!

Well, there was no way I intended to spend the weekend cooped up in Ron’s gilded cage. I’d make him take me out, with me as the girl and him as the guy - after all, isn’t that what he asked for in his email? And maybe, during the day, I’d try to teach him a few tricks of the trade, help him try to find something in his closet that would help to disguise his more masculine qualities, although I was no miracle worker. And there was one thing I’d spotted in his closet that I wanted to try on myself….

Half an hour later, wigged and made up, I returned to the bedroom and fished some lingerie and stockings out of my suitcase. It always felt so good to put them on! I was just about to return to The Closet for my outfit when I heard a tap on my door. “Are you decent?” Ron asked.

“No, but come on in.” I struck a Victoria Secret model’s pose as Ron opened the door and peeked in.

“Oh my God, you are so hot! What I’d give to have a body like that.”

“You’re not so bad yourself, Mister. And since you’re gonna be wearing the pants around here, I’d say your body will definitely do.” I walked over to him, stood up on my tiptoes and kissed him lightly on the lips. “There will be some compensations for you, if you’re nice to me….”He pressed himself against me, and I could feel his rock hard member raging against my tummy. “Goodness, maybe I don’t want you to be nice to me.” I looked up at him and closed my eyes, waiting for him to kiss me. He did, a nice kiss, but I could tell that he was distracted by something. “What’s wrong?” I asked him.

“Missy, while I was waiting I turned on the evening news. There’s a picture of a woman the police are looking for, actually they’re saying she’s transgendered, and she’s very pretty, and she looks so like you. It’s about something that happened at the Intercontinental while you were staying there….” I sank down onto the bed in my slip and stockings, trying to think of what to say. “Missy, you don’t have to worry about me. You’re safe here, and you can stay as long as you like. I just need to know what happened. Maybe I can help you?”

How did I deserve such a man? After the way I’d treated him, no less? I started to shake, then I started to cry, a real woman’s tears, as he sat down beside me and hugged me. “I’m so sorry Ron, I shouldn’t have come here. I don’t want you to get involved,” I sobbed.

“Tell me what happened, baby. Just tell me what happened.”

“Okay, I will, but give me a minute to get dressed and do something about my mascara.” Ron slipped out the door, and I went to the bathroom to repair the damage to my face. I was about to put on the outfit I’d hung in the closet when I had an idea: why not show Ron what Gregg had done to me, by putting on my ruined dress? I fished it out of my suitcase and tugged it on. My whole body shuddered when I zipped it up in the back. Actually, I was surprised to see that my dress didn’t look that bad: there was a rip across the bodice, but nothing that a good seamstress couldn’t cure. I found my stilettos to complete the outfit, and hesitantly waked down the long oak staircase.

Ron was waiting for me in the living room, with a bottle of wine and two glasses. He poured one for me, and waited for me to speak after I gulped it down. “What happened to your dress?” he asked.

It just came pouring out, beginning with how bummed I’d been when Ron didn’t show up (he tried to apologize again but I just plowed on) then the sudden flirtation with Gregg, how strong and forceful he’d been, and how grateful I’d been to have another man in my life. I described our meeting in the lobby bar, how handsome Gregg was, and how he was able to get me to reveal intimate details during our brief conversation, and how I got a little drunk and let him walk me to my room. I even told Ron about the elevator kiss, and how I thought Gregg was about to kiss me again when he savagely attacked me once he got into my room.

“What did you do?” he asked in astonishment.

“It was pure instinct. I fumbled around and found a pair of sharp scissors on the nightstand. He was strangling me! But I managed to stab him in the side, and he let go enough for me to get away, and then I went for his throat, I didn’t mean to kill him but that’s what happened.”

“Christ! He died right there in front of you?”

“It was horrible. I was about to call the police, but then I thought about all the publicity, which would ruin my career – can you imagine? Out-of-town executive dressed as a woman kills Craigslist killer? So I thought about it, and I’m really ashamed of this, but I found a way to get his body out of my room and down the hall, and then I checked out of the hotel the next day, but not before I lied to the police when they came knocking on my door. I’m so fucked,” I said, and the tears started again.

Ron took me in his arms and hugged me tight, rubbing my shoulders. “Baby, you did nothing wrong. Okay, maybe you should have told the police what really happened, but after what you’d been through, nobody could blame you for that. What you did was self-defense, anyone can see that, and once you tell the police what really happened, you’ll be in the clear.”

“That’s just it, Ron. I can’t tell them now. Maybe I should have right after it happened, but now that I’ve lied to them, they might never believe me. I could get charged with murder! And even if I don’t, once the story hits the newspapers, I’ll be totally fucked.”

“Okay Missy, let’s try to forget about it for tonight. You’re totally safe here. And this time, you’re going to get a home-cooked meal.” I followed him into the gourmet kitchen, and helped him set the table, but he was clearly in his element. When we finally sat down to dinner, it was as elegant as the last time, a delicious pasta that I’d never had before. After my fourth glass of Chardonnay, I was feeling no pain, and Ron wisely waved me off when I offered to help with the dishes.

When he was done, I followed him up the stairs to the bedroom. No words were said, but I was sure that we were going to spend the night together, in his bed, and I went all out with my babydoll nightie and matching white stockings. I snuggled under the covers and waited for Ron to join me. But when he came to the door, in long pajamas, he only wished me a good night, turned out the light, and disappeared.

* * *

Despite my disappointment, I slept soundly through the night, and was awakened by the smell of bacon and coffee being prepared downstairs in the kitchen. I pulled the robe in the bathroom over my scanty sleepwear, put on my wig and a touch of makeup, and tiptoed down the staircase to the kitchen in my stocking feet. Standing at the sink with her back to me was a large woman, with an apron tied over her shirtdress. She was humming a refrain from Don Giovanni in a deep voice.

Of course the woman was Ron. I didn’t want to embarrass him, although the sight was so ludicrous that it was hard not to laugh. So I just stood there silently, waiting for him to turn around. When he did, he was so startled to see me that he dropped a dish, which shattered on the hardwood floor. I watched as he got down on his knees and started picking up the broken pieces. I stooped down too, gathering my robe around my knees, and began to help him. Our eyes met, and in spite of myself, I started to giggle. Then he started to laugh, a deep man’s belly laugh, and soon we were rolling around on the floor, in our women’s clothing, carried away by the absurdity of it all.

“I didn’t know you were here,” he finally said, a bit sheepishly. “I wanted to surprise you with breakfast in bed.”

“I’m sorry I startled you! What’s your name?”

“Huh?”

“Sweetheart, if we’re gonna be sisters today, you have to have a girl’s name!”

“Would you really like me to do that?”

“Well, I am your guest, and it is your house, and at the moment you definitely don’t look like a Ron. So unless you’re happy with Ronette, I suggest you think up a nice name for yourself, something pretty. Only you can’t use Missy, I’ve taken it already.”

Another belly laugh from my still-to-be-named hostess. “Thank you, Missy, for being so understanding. I’ve always like the name Caroline….”

“Then Caroline it shall be. So tell me, Caroline, are you a fan of fifties TV shows?”

“I don’t know, why?”

“Because in that outfit you’re wearing, you look like a cross between June Cleaver and Harriett Nelson! Honestly, where did you get that dress? And those shoes?”

* * *

For the rest of that morning, we sat at Caroline’s kitchen table, eating a delicious breakfast and chatting away like two sorority girls. Once I’d gotten over the shock of seeing Ron in women’s clothing, I found myself wanting to help Caroline, and I’m sure her head was ready to explode after the umpteenth tip about hair (her wig was way too long for a woman her age) makeup (not too bad, actually) and clothing (tragic, see above). I asked her how she’d managed to accumulate the incredible stash of clothes, shoes and accessories in her closet.

“Online, all of it.”

“Have you tried all of them on?”

“Yes, and about half of them don’t even fit! Or at least they don’t look very good on me. I’m so hopeless, Missy! That’s why I was hoping you could help me.”

“Listen, I totally understand how hard it is to get started. My big breakthrough came when I finally got up the courage to go out shopping as a woman. You really have to try on a dress to see how it drapes, especially when you haven’t got a woman’s body to begin with. There’s been a lot of trial and error for Missy here, believe me.”

“I could never do that!”

“It’s hard at first, but once you get used to it, it’s so much fun! But let’s be honest, Caroline: I’m really lucky with my body. And as pretty as you are as a girl, well, what I’m trying to say is once you put on heels like the ones you’re wearing, you’re going to tower over everybody, and unless we can find something that sort of masks those big shoulders of yours, it’s gonna be awfully tough for Miss Caroline to make it in the big city.”

“I understand, and after seeing you, I totally get that I’ll never be able to pass the way you do. But to tell you the truth, I really liked being the man on your arm the other night. In fact, I was hoping we could do that again, tonight.”

“I’d love it!”

“Except now that you’re a wanted criminal, or witness, or whatever the cops are looking for, won’t that be terribly risky?”

“Not if you let me borrow that killer blonde wig in your closet.”

* * *

I will never forget the excitement of preparing for my first ever Saturday night date. This was no Craigslist one-night stand in the middle of a business trip – it was an honest-to-goodness weekend date with a rich, handsome man who knew my most intimate secrets. Looking back, I didn’t know quite as much about Ron as I should have, which would soon become all too deadly…but that evening, as I shaved my body, made up my face and got ready to dress myself, my heart was full.

One of the things I did learn about Ron – or Caroline – that afternoon is that he/she was very accomplished with a needle and thread, and the little black dress which I’d bought to wear for him on Wednesday was waiting for me in the closet. But first, I tried on Caroline’s gorgeous blonde wig – it was a bob, slightly longer than my brunette look, and the transformation was stunning. I went with my new garterbelt and stockings again, then a bra and panties, my black slip, and finally my new dress. I already knew it looked good on me, but the sight of the blonde in The Closet’s full length mirror took my breath away. I couldn’t take my eyes off her as she stepped into her stilettos and tugged her clingy dress down over her knees. She was a knockout, and she was me!

Ron was himself again, gorgeous in an impeccably tailored gray suit, crisp white shirt and subdued tie. Since we’d spent the entire day indoors chatting away as girls, I didn’t realize that the weather had taken a nasty turn until Ron got his Burberry’s coat out of the hall closet. My dress had cap sleeves, and my pashmina shawl would be no match for the Chicago winds. Not a problem: Ron accompanied me back to The Closet and helped me select a cute black jacket that was a tad big for me, but went perfectly with my dress. Then it was off to Morton’s in his BMW, a few short blocks away. Ron must have been a regular, because as soon as the maître d saw him, we were ushered to a romantic little booth in the crowded restaurant.

Ron’s reputation as a connoisseur of expensive wines preceded him, and the sommelier materialized with a bottle of Sonoma Coutrer. After the uncorking and tasting ritual, we settled into easy conversation about the menu. A waiter appeared with a trolley full of meat and fish samples, even a live lobster, and we each ordered filet mignon with a side of creamed spinach to split. It must be obvious that every detail of that evening is engraved in my mind, including two snippets of conversation that loom large in my memory.

At one point, I asked Ron about what happened to his marriage. I assumed he’d tell me that his wife was freaked out about his dressing as a woman, and left him over it, but that was only part of the story. It seems that Ron had always had a gay streak, which he mostly suppressed over the years, but yielded to from time to time. There is a robust gay community in Chicago called Boys Town, and Ron had discovered the delights of bottoming there.

I wasn’t shocked, because I’d played on the same turf. But I’d always been dressed as a woman, which somehow didn’t seem gay to me. Sitting there in Morton’s, in a beautiful dress, on a date with a handsome man, in my mind I was really a woman, and I’d convinced myself that sex with a man was a natural act.

At another point, we talked about the fix I was in. Ron had learned a bit more about the police investigation. It seemed that the tgirl Gregg killed at the Sheraton - and me - weren’t his only victims: over the past six months, he’d left a trail of transgendered women whom he’d robbed in their hotel rooms. The police speculated that he singled out transgendered women from out of town because he knew that they would be less likely to complain to the police, which would force them to reveal to the world that they were crossdressers trolling for sex with men. I had to agree with them!

Fortunately, the name of the man from Los Angeles who had been interviewed in his room at the Intercontinental the night of the murder had not been picked up by the media, and I was pretty sure that if I resurfaced as a male on Monday and flew back to Los Angeles, my troubles would be behind me.

* * *

After a long, lovely dinner, Ron drove me back to his home. On the way, told him that I hoped he’d feel comfortable staying in his bedroom with me. “I promise I won’t bite,” I teased him.

Ron squeezed my knee once again, and he was delighted to discover a garter clipped to my stocking. “Only if you let me undress you.”

“I think that can be arranged,” I said. By that point, after all the frustrations of the past week, I was incredibly horny, and more than a little drunk, and I was bound and determined to take Ron to bed. When we got back, I asked him to give me a moment, and I closed myself in the bathroom to freshen my makeup. The blonde in the mirror looked pretty and confident.

Ron was waiting for me in bed, his clothes neatly folded on top of the dresser. The lights were turned down low. Without a word, I kicked off my heels, pulled back the covers, and slithered in next to him. He kissed me, a long, lovely kiss, then he reached behind me and started unzipping my dress. I was docile and willing as he gently lifted it over my head, and he caressed my silky slip before he took that off too. He seemed surprised that I wasn’t bound up in Spanx or a body briefer, but after years of dieting, situps and crunches, I did quite well with a padded bra and panties, and the payoff came that night as Ron continued to undress me. While he did, I started to push his hot buttons, nibbling and breathing in his year, teasing his nipples with my long fingernails, and gently stroking his penis. He moaned when I played with him, but he wasn’t getting hard.

Meanwhile Ron was rubbing my legs in my nylons, which was incredibly arousing. I knew that I couldn’t hold out much longer. “What’s wrong, baby?” I whispered in his ear.

“I’m sorry, Missy. I just can’t.” I knew from the night before, when I’d kissed him before dinner, that his body was capable of a rock hard erection, and I wasn’t going to give up on him.

Maybe a little crossdressing would help him? I sat up and slowly unclipped a nylon from its garters. After I took it off, I started rolling it up one of Ron’s legs. He was laying back on the bed, and a look of sheer ecstasy came over his face as I slid it higher and higher. I unclipped my other nylon too, and as I rolled it on him, his penis came to life before my eyes. I’d never seen anything like it: one minute it was soft and tiny, and the next minute it was standing straight up, at full attention, ready and waiting for me to climb aboard.

My condoms were somewhere in my suitcase, but between the two of us, there was plenty of pre-cum to spread around…before Ron knew what was happening, I impaled myself on him, straddling him like a horse, and started riding him up and down, up and down. I was so ready, and he was too. I’d never made love to a guy without protection before, and he felt so hot inside me! When he came, I could feel his jism spurting deep within me, and then I came, a gusher that splashed all over his chest as the sweet waves of pleasure curled my toes.

When we were done, I lifted myself off and snuggled next to him. “Sorry about the mess,” I sighed.

Ron didn’t say anything for some time. When he finally spoke, I thought me might be crying. “Missy, I’m so sorry.”

“Sorry about what? That was the best sex I’ve ever had.”

“Me too, but there’s something I haven’t told you.”

“What, that you want to be a girl? I can live with that….”

“No, that’s not it. I have H.I.V.”